The Royal Family‘s annual gathering at St Mary Magdalene Church in Sandringham is always a highly anticipated event.
It gives family members a chance to dress in their best attire and greet the public, who gather eagerly outside.
And two royals have left a lasting impression: Diana, Princess of Wales, and Sarah, Duchess of York.
Together, they turned the walk to the church into a stylish showcase – displaying a variety of seasonal outfits.
In December 1988, the duo made their first joint appearance at Sandringham, radiating joy as they arrived side-by-side.
Diana exuded elegance in a striking Catherine Walker coat-dress, while Sarah complemented her in a peplum skirt suit and fur-trimmed cossack hat.
Their triumphant appearance would set the tone for the years that followed.
In December 1988, Diana, Princess of Wales, and Sarah, Duchess of York, made their first joint appearance at Sandringham, radiating joy as they arrived side-by-side
The relationship between Diana and Sarah, known as Fergie, began long before their marriages into the Royal Family, as they were fourth cousins.
Their mothers attended school together and the two women had known each other since their teenage years. However, their friendship blossomed when they reconnected in 1980, when Diana was 19 and Sarah was 21.
After Diana married Prince Charles in 1981, she introduced Sarah to her brother-in-law, Prince Andrew. The Duke and Duchess of York said ‘I do’ in 1986.
As the two women rose to worldwide fame, they found unique support in one another.
However, according to author Penny Junor, Diana was envious of Sarah’s popularity.
In her 1987 book, Charles: Victim or Villain, she wrote: ‘The arrival of Fergie into the royal circle was a mixed blessing for the Princess. On the one hand, she was someone closer to her own age and an ally. But she was also a rival.
‘In the early days, Fergie was popular. She was like the girl next door, undaunted by protocol, relaxed, irreverent and determined to have fun: people talked about her being a breath of fresh air.
‘Diana, who had never been confident at the best of times, felt doubly insecure. As she later admitted, “I got terribly jealous”.’
Interestingly, Sarah has since admitted to imitating her friend in social situations. During her 2023 podcast, Tea Talks with the Duchess and Sarah, she recalled: ‘I remember when I first became a princess with Duch [Diana], and I watched her work a room.
‘And I just copied her. I mirrored her, how she did it because she was just incredible. She just immediately went in with her heart. Full heart, full energy and she left everything outside the door.’
Sarah also appeared to echo Diana’s flair for fashion, frequently selecting attention-grabbing ensembles for her engagements.
And Christmas Day provided the perfect opportunity for both women to present their most impressive attire.
In 1991, Diana brightened the misty landscape with a distinctive two-tone suit by Catherine Walker, complete with matching accessories
Sarah jubilantly followed, wearing a winter-ready ensemble, incorporating a houndstooth jacket and beret
Diana set the tone for royal fashion, once turning heads in a chocolate-brown ensemble, featuring a fur-lined coat layered over a dress with a thigh-high slit
In 1990, Diana donned a daring purple tweed coat dress, featuring striped lapels, buttons and cuffs, paired with a Philip Somerville hat for a glamorous aesthetic. Sarah, meanwhile, embraced the festive spirit in a vibrant red coat and cosy fur hat
After her separation from Charles in 1992, Diana continued to attend royal events – famously making a powerful statement in red
Beyond her humanitarian work and marriage to Charles, Diana’s enduring legacy has been her impact on fashion.
As a princess, she adhered to royal protocols yet managed to express her individuality through bold colours and distinctive patterns.
She worked with several top designers of her time, including Bellville Sassoon, Victor Edelstein and Catherine Walker – the latter now a favourite of the Princess of Wales, Kate Middleton.
In 1990, Diana donned a purple tweed coat dress, featuring striped lapels, buttons and cuffs, paired with a Philip Somerville hat for a glamorous aesthetic.
Sarah, meanwhile, embraced the festive spirit in a vibrant red coat and cosy fur hat.
The following Christmas, Diana brightened the misty landscape with a distinctive two-tone suit by Catherine Walker, complete with matching accessories.
Sarah jubilantly followed, wearing a winter-ready ensemble, incorporating a houndstooth jacket and velvet beret.
Reflecting on their bond during an episode of her podcast, she described the Princess as the person who could make her laugh more than anyone else. ‘We loved each other with all our hearts,’ she said.
After her separation from Charles in 1992, Diana continued to attend royal events – famously making a powerful statement in red on the steps of the church.
Last Christmas, the Duchess made a memorable return to Sandringham for the first time in over three decades
In contrast, Sarah did not appear at Sandringham following her own separation from Andrew in 1992.
However, last Christmas the Duchess made a memorable return to St Mary Magdalene Church for the first time in more than three decades.
Wearing a hunter-green coat by Holland Cooper with a peacock-feather headband, she warmly greeted members of the public who had gathered to see the Royal Family.
Sarah shared her delight to have received an invitation from King Charles, posting on X: ‘We are enjoying each other’s company and feeling grateful today. I hope everyone has a wonderful day. Happy Christmas to anyone who celebrates and season’s greetings to all!’
